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Winchester vacation rentals

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Top-rated vacation rentals in Winchester

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Chalet in Davis

4.85 out of 5 average rating, 155 reviews

Big, Bright SLOPESIDE Ski Chalet, Outdoor Hot Tub!

Don't be fooled by other misleading "slopeside" listings! This gorgeous 5-bedroom lodge is adjacent to Timberline's Winterset ski run — perfect for families. Outdoor hot tub. Large open floor plan, plus separate living area downstairs. Two gas fireplaces. Master suite has Jacuzzi for 2. Wifi, 2 flatscreen HDTVs. Please don't request to book this chalet unless you have at least 3 positive reviews on Airbnb. If you don't have 3 positive reviews, your request to book will be respectfully declined

Chalet in Mercersburg

4.94 out of 5 average rating, 105 reviews

Amazing Whitetail Ski Holiday and Mountain Retreat

Welcome to our beloved Mountain home. Located at Whitetail resort you can walk to the slopes and enjoy the après ski in our beautiful cozy house with cabin feel. Perfect ski holiday, weekend getaway, or place to work remotely with high-speed internet. Only 1.5 hours from DC & Baltimore. This is the perfect place to escape the city, connect with nature and recharge. A place to build up fond memories. All season adventures, enjoy skiing, swimming, hiking, golfing, fishing, lakes and local farms.

Home in Basye

4.94 out of 5 average rating, 139 reviews

Romantic Treetop Retreat: Hot Tub•King Beds

Brand New Listing! Completely renovated cabin sits up among the trees. This comfy and stylish cabin is the perfect place to visit Bryce Resort (1.5 miles) and the many wineries and hikes nearby. The hot tub is the ideal spot to relax and breath the mountain air. Multiple outdoor spaces and fire table to enjoy. New Memory Foam beds, 65 inch Tv over the electric fireplace, rainfall shower head, stocked kitchen Every inch of the house has been designed for the perfect romantic or family getaway.

Cabin in Luray

4.95 out of 5 average rating, 140 reviews

❤️️Wildflower Cabin❤️️ A Luxury Riverfront Retreat

*Come in and relax in this tranquil, peaceful hideaway. *Newly renovated cabins on Shenandoah River. *100 feet riverfront on a 2 acre property *AC/heat, satellite Wifi, fresh linens, towels, DVDs, board games. *Full kitchen w/ utensils, microwave, toaster, K-cups. *Secluded, close tohiking, caverns, wineries, and river adventures.*Dog friendly (extra fee of $40/dog/stay and will be asked for after booking, not included in booking fees) ! *King-size bed in bedroom, queen sofa bed in living room.

Cabin in Basye

4.99 out of 5 average rating, 187 reviews

“Lazy Basye” Cabin-Hot tub, 2 King/1 Queen/2 bunks

Bryce Resort (ski/golf/lake/bike park) in the Shenandoah! Ideal setup- 2 indoor living spaces! 4 BR/3 full bath. Fully equipped kitchen, memory foam mattresses (2 king/1 queen/2bunks), electric fireplace, hot tub, outdoor fire pit, screened porch w/ dining/sectional/TV. Gas grill, deck dining & views! Rec room w/ views, pool table, foosball, Golden Tee, 65" TV, sectional, games! Multiple decks/patio, fast WiFi, private parking, full size W/D, 4 smart TVs. Must be 25 to book. Holidays-3 night min

Home in Elkton

4.94 out of 5 average rating, 163 reviews

Hottub 5 acres, Great hiking,The best views around

Stony Creek Lookout is a one-of-a-kind luxury retreat perched in the serene seclusion of the mountains.Brand new complete renovation, modern amenities, hot tub, sizable elevated deck, video/board games, theatre room, kayaks and high quality furnishings !This extraordinary stay adjoins the Shenandoah NatlPark with the best views in the Shenandoah Valley, hike out your back door. Pet friendly, 5 min from Massanutten 4 season resort, Shenandoah River & much more. Great Wifi & cell service! 5 TVs

Home in McHenry

4.9 out of 5 average rating, 127 reviews

Ski/in Ski/out Luxury Home Voted #1

For Summer or Winter---The Best House and LOCATION in Deep Creek Lake- Large level lawn with a sandy beach. Private dock slip. Views on both sides- across street from chairlift. Watch your family and friends ski and ride down the mountain from the glass enclosed 45' x25' open great room at the party lodge located at base of chair 5. Luxury with gourmet kitchen.- lots of room for parties. 70" flat screen, two wet bars, pool table, three indoor Jacuzzis, hot tub, fire pit--- many extras!

Home in Edinburg

4.98 out of 5 average rating, 369 reviews

The Burrow ~ Our guest reviews say it all!

Indulge in a serene retreat at this charming countryside residence, perfect for a delightful getaway or a quick overnight stay. Just a 4-minute drive with two easy turns from I-81, this cozy home promises tranquility and relaxation. Begin your day on the inviting porch, soaking in the sunrise, setting the tone for a peaceful escape. Explore attractions such as hiking trails, enchanting caverns, or indulge in the local offerings of nearby wineries. A short stroll reveals Dee and Kenn's home.

Cabin in Shenandoah

4.78 out of 5 average rating, 442 reviews

Shenandoah Sunsets~Breathtaking Views~ New Hot Tub

*Weekends fill fast, but we have great weekday rates! --Breathtaking mountain top cabin with private river access • 180 degree sunset views from 4 decks • Minutes from downtown Luray & Massanutten Resort • Backs to 400 acres of private woodlands • Fully equipped & stocked kitchen • Gas Fireplace • Grill • Onsite washer & dryer • Queen sofa bed • Foosball table • Satellite internet • Smart TVs • Paved driveway • Extensive DVD collection + games • Come feel the amazing mountain top breezes

Cabin in Harpers Ferry

4.8 out of 5 average rating, 416 reviews

Cozy Cabin Hidden Away on a Lake!

MOUNTAIN MAMA VACATION HOMES The perfect getaway for any season! Enjoy the lake views inside next to a roaring fire, or in the summertime take the kids for a swim in the shallow water just off your private beach. Relax in the hot tub set in the back deck as the sun sets over the lake and the stars start to come out. Make every night movie night on the 50" 4k TV. Whether you want to stay in or see the area, this cabin has something for every member of the family!

Cabin in New Market

4.93 out of 5 average rating, 142 reviews

Views! Hot Tub! Fireplace! Tranquil Mount Escape

Experience the ultimate mountain retreat in Newmarket, VA!! Enjoy spectacular views of the valley from the deck's hot tub or relax on the beautiful screened porch. The interior has been completely remodeled, featuring a wood-burning stove and high-speed internet. Surrounded by the George Washington National Forest on three sides, adventure awaits just steps away. Book your stay today and immerse yourself in the tranquility of the mountains. 4WD/AWD required.

Cabin in Rileyville

4.93 out of 5 average rating, 126 reviews

A+ Privacy & Views | HotTub + Firepit + BBQ | Pets

Secluded mountain cabin with 2 kings, hot tub, fire pit & panoramic views! ★ "Amazing place… the views are breathtaking." ☞ 2 level deck w/ mountain views ☞ Complimentary SUV provided ☞ Hike to waterfall (20 mins) ☞ Fully equipped + stocked kitchen ☞ Patio w/ BBQ grill + dining ☞ 50” Smart TV w/ Netflix ☞ Indoor wood fireplace ☞ Pet friendly* 20 mins → DT Luray (cafes, dining, shops) 30 mins → Shenandoah National Park

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Winchester vacation rentals

Laptop-friendly workspace

Stay near Winchester's top sights

Museum of the Shenandoah Valley72 locals recommend

Shenandoah Valley Discovery Museum34 locals recommend

Bonnie Blue Southern Market & Bakery28 locals recommend

Bright Box Theater28 locals recommend

Martin's Food25 locals recommend

Old Town Winchester25 locals recommend

Other great vacation rentals in Winchester

Cabin in Linden

4.87 out of 5 average rating, 94 reviews

Skyland Hideaway | Mountain Cabin w/ Hot Tub

Home in Sabillasville

4.93 out of 5 average rating, 107 reviews

Stoney Spring Overlook

Cabin in Augusta ( Capon Bridge)

4.96 out of 5 average rating, 142 reviews

Nirvana, Mountain View

Cottage in Harpers Ferry

5 out of 5 average rating, 58 reviews

Cozy Mountain Cottage Perfect for Friends & Family

Cabin in McHenry

4.84 out of 5 average rating, 62 reviews

3+acres-petfriendly-hottub-fireplace-pool table

Vacation home in Luray

4.83 out of 5 average rating, 119 reviews

★ Cozy Country Cabin ★ near Luray & hiking trails!

Home in McGaheysville

4.96 out of 5 average rating, 48 reviews

In Resort- Family fun- Kids Suite-Game Room

Home in Smithsburg

4.96 out of 5 average rating, 116 reviews

The Great Escape Lodge ~ Exquisite Mountain Views

Quick stats about vacation rentals in Winchester

Total rentals
100 properties
Total number of reviews
6.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
90 properties include access to wifi

Frequently Asked Questions

Are there house rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 10 house rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Winchester?
Experience the best of Winchester with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Winchester have wifi?
Absolutely! We offer over 40 apartment rentals with wifi in Winchester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winchester have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly apartment rentals in Winchester?
Four-legged friends are welcome in Winchester. Choose from more than 20 apartment rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Winchester?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

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